(S)-1-((benzyloxy)carbonyl)pyrrolidine-2-carboxylic anhydride | 70290-86-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-1-((benzyloxy)carbonyl)pyrrolidine-2-carboxylic anhydride
• 英文别名: 1-O-benzyl 2-O-[(2S)-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl] (2S)-pyrrolidine-1,2-dicarboxylate
• CAS: 70290-86-7
• 化学式: C₂₆H₂₈N₂O₇
• 分子量: 480.518
• InChiKey: NRAXJNGZKRLMHS-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-1-((benzyloxy)carbonyl)pyrrolidine-2-carboxylic anhydride 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 N-苄氧羰基-L-脯氨酸
  参考文献：
  名称：

  Light-Enabled Synthesis of Anhydrides and Amides

  摘要：

  Recently, we have demonstrated that the photogeneration of Vilsmeier-Haack reagents is possible using only dimethylformamide (DMF) and tetrabromomethane (CBr4) in the bromination of alcohols. Extending these findings to carboxylic acid substrates has produced a mild and facile approach to the in situ formation of symmetric anhydrides, which were conveniently converted to amide derivatives in a one-pot process. The efficient protocols discussed herein are marked by use of UVA LEDs (365 nm), which have reduced the reaction times and come with a low setup cost.

  DOI：

  10.1021/acs.joc.5b00003
• 作为产物：
  描述：

  N-苄氧羰基-L-脯氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (S)-1-((benzyloxy)carbonyl)pyrrolidine-2-carboxylic anhydride
  参考文献：
  名称：

  Synthesis of novel chiral polyamide macrocycles containing pyridyl side-arms and their molecular recognition properties

  摘要：

  Seven novel C-2-symmetrical macrocycles containing pyridyl units have been prepared by the cyclic condensation of homochiral diamide intermediates with 2,6-pyridinedicarbonyl dichloride under high dilution at room temperature. The molecular recognition of these homochiral macrocycles for amino acid derivatives has been characterized by various spectroscopic methods such as IR, FAB-MS, fluorescence and UV-vis. The macrocycle 11 exhibited significant chiral recognition towards the enantiomers Of D- and L-alanine methyl ester hydrochlorides for which association constants have been determined. Molecular modeling was also used to simulate the interaction mode between the hosts and the guests. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00173-3

文献信息

• Yb(OTf)₃-Catalyzed Desymmetrization of <i>myo</i>-Inositol 1,3,5-Orthoformate and Its Application in the Synthesis of Chiral Inositol Phosphates
  作者：Laxmansingh T. Padiyar、Medel Manuel L. Zulueta、Narayana Murthy Sabbavarapu、Shang-Cheng Hung

  DOI：10.1021/acs.joc.7b01919

  日期：2017.11.3

  A variety of inositol phosphates including myo-inositol 1,4,5-trisphosphate, which is a secondary messenger in transmembrane signaling, were selectively synthesized via Yb(OTf)3-catalyzed desymmetrization of myo-inositol 1,3,5-orthoformate using a proline-based chiral anhydride as an acylation precursor. The investigated catalytic system could regioselectively differentiate the enantiotopic hydroxy

  各种肌醇磷酸酯，包括肌肉肌醇1,4,5-三磷酸，它是在跨膜信号传导的第二信使，经由被镱（OTF）选择性地合成3的催化的desymmetrization肌醇肌醇1,3,5-使用原甲酸酯脯氨酸基手性酸酐作为酰化前体。所研究的催化系统可以区分区域选择性的对映羟基肌肉中的手性助剂的存在肌醇1,3,5-原甲酸酯。这个关键步骤，以产生适当保护的手性肌醇肌醇衍生物在这里被描述为一种统一的方式来肌醇磷酸酯的访问。
• Hauzer, Karel; Servitova, Linda; Barth, Tomislav, Collection of Czechoslovak Chemical Communications, 1982, vol. 47, # 4, p. 1139 - 1148
  作者：Hauzer, Karel、Servitova, Linda、Barth, Tomislav、Jost, Karel

  DOI：——

  日期：——
• Synthesis of novel chiral polyamide macrocycles containing pyridyl side-arms and their molecular recognition properties
  作者：Xiao Chen、Da-Ming Du、Wen-Ting Hua

  DOI：10.1016/s0957-4166(03)00173-3

  日期：2003.4

  Seven novel C-2-symmetrical macrocycles containing pyridyl units have been prepared by the cyclic condensation of homochiral diamide intermediates with 2,6-pyridinedicarbonyl dichloride under high dilution at room temperature. The molecular recognition of these homochiral macrocycles for amino acid derivatives has been characterized by various spectroscopic methods such as IR, FAB-MS, fluorescence and UV-vis. The macrocycle 11 exhibited significant chiral recognition towards the enantiomers Of D- and L-alanine methyl ester hydrochlorides for which association constants have been determined. Molecular modeling was also used to simulate the interaction mode between the hosts and the guests. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Light-Enabled Synthesis of Anhydrides and Amides
  作者：Terry McCallum、Louis Barriault

  DOI：10.1021/acs.joc.5b00003

  日期：2015.3.6

  Recently, we have demonstrated that the photogeneration of Vilsmeier-Haack reagents is possible using only dimethylformamide (DMF) and tetrabromomethane (CBr4) in the bromination of alcohols. Extending these findings to carboxylic acid substrates has produced a mild and facile approach to the in situ formation of symmetric anhydrides, which were conveniently converted to amide derivatives in a one-pot process. The efficient protocols discussed herein are marked by use of UVA LEDs (365 nm), which have reduced the reaction times and come with a low setup cost.